For anyone tired of doing the standard 9-to-5 and sitting at the same cubicle every day, the idea of joining the growing movement of contingent workers might seem like a dream: blissful, yet completely unachievable.

After all, one of the biggest challenges people face is figuring out to take the leap from your full-time corporate gig into the contingent workforce. But with up to 30 percent of workers now working in freelance, consulting, independent contracting or virtual roles, it’s becoming less of a distant dream and more of a reality for many people.

i should know; i’m one of them

Earlier this year, I left my job with LinkedIn to travel the world with my wife and one-year-old son while building out a freelance content writing business. In May 2017, we flew to Paris, saddled up in an Airbnb for a month and explored the city every day while working in cafes and during my son’s naps to create a business - and a lifestyle - that would allow me to be more active as a father, while also providing my family a once-in-a-lifetime opportunity to explore the world.

Shortly into our trip, I wrote a post on LinkedIn about my decision to leave my dream job in pursuit of a dream life. The post took off (as of writing this, over 33,000 people have read it), and the reception from people all across the world was unbelievable. I received so many encouraging messages, heard so many stories of people who had done the same thing years before and never regretted it.

But I also had a number of readers really interested in learning exactly how I made it happen, and how they could do the same thing.

After all, before the start of 2017, my writing experience was limited to some teen-angsty poetry I wrote in college. (Which I’m pretty sure still exists somewhere in the bowels of the internet. Please, I’m begging you, don’t Google it.)

So people were genuinely intrigued: how does one build out a side business to a point where you can easily transition to a contingent worker, while also managing a full-time job? And so that’s what I’m covering for you here today. 


first, here’s why becoming a contingent worker is more realistic than ever

It wasn’t too long ago that remote work - whether it be as a freelancer, consultant, contractor, or virtual employee - was pretty fringe. People dreamed of breaking free from the rat race for decades, but a couple factors are contributing to contingent work becoming more realistic for more people each year as companies begin to accept that remote work is the future. In fact, Randstad estimates that by 2025, 85 percent of businesses will be committed to supporting a contingent workforce. Pretty amazing, right?

So, what’s motivating businesses to adapt and be more receptive to non-traditional workers?

it’s more cost-effective than hiring full-time employees.

Contingent workers don’t come with all the overhead costs associated with supporting a team of full-time employees. Businesses pay contingent workers on a per-project or hourly basis, which means companies save in two important ways:

  • First, by cutting out the expensive benefits and perks companies need to remain competitive in today’s race to attract and retain best-in-class talent.
  • Second, by paying only for the work completed. When work slows down for a full-time, salaried employee, the company still pays for that time. Whereas contingent workers allow businesses to scale their workforce up or down based on company need.

That’s why it should come as no surprise that 24 percent of companies utilizing contingent workers cite cost reduction as a primary reason for maintaining a flexible staffing model. 

there’s huge demand

Not only are businesses seeing the benefits of hiring contingent workers, but the freedom and flexibility attracts more and more full-time employees every year, too. In fact, 70 percent of workers in Canada said they would quit their current full-time job for a remote-working opportunity. Workers shared the top five reasons contingent work is of interest. Here’s what they said:


I know I can personally relate to all five of these. 

Like most of Randstad’s survey respondents, I too was primarily motivated by the flexibility and control of my hours. At LinkedIn, I often left the house before my son woke up in the morning and had only a couple hours to spend with him in the evening. And as I’m sure many other parents with little ones at home can relate, I was feeling the pangs of FOMO every time my wife sent me pictures of my son playing at the park while I trudged away at the office.


My wife, Hailey, and 1-year-old son, Owen.

So, I decided to make a change. And you can, too. Here’s how.

how to figure out what contingent career makes the most sense for you and your experience

I launched a career in content creation because I enjoy writing and felt my combined experience in recruiting and customer success gave me a unique perspective on the world of talent acquisition. But of course, your skills and experience may take you down a completely different path. You might have some web design experience, or a passion for social media marketing, or even just a solid background in customer support. The important thing is, finding a career where your passion intersects with flexibility and mobility.

Try these strategies for uncovering the right contingent career path for you:

1. find people doing what you love on linkedin

With over 500 million members around the world, LinkedIn should be your go-to resource for gauging whether there are people pursuing your passion as a contingent worker.  And the best part is, you don’t need an upgraded account to find and message the people in your network. 

Here’s how to do it:

  • Use Boolean logic to build a search string for your area of interest plus “freelancer OR consultant OR contractor”

  • Narrow your results to 1st-degree connections.

  • Send 1st-degree connections a quick message (for free) asking if you might be able to send them over a couple questions as you’re considering embarking on a career in the same field and would love their input and advice. NOTE: I’ve received several such emails since launching my business and am always happy to provide my thoughts. No matter who you contact, make sure your patient and give them some time to respond - it’s likely they have a lot going on while managing their own business.

2. check out

If you’re not familiar with the term “digital nomad,” it’s a catch-all phrase for people who have made the leap from their full-time corporate careers to remote working around the world.  (They’re the ones mostly responsible for all those drool-worthy photos of young people working on a laptop on the beach or a remote mountaintop that you’ve likely seen all over the internet.)

I like to fancy myself a digital nomad (even if it is a bit overused nowadays) given my location independence and business I’ve created for myself. And that’s why I’m a fairly religious follower of the subreddit for digital nomads over on A quick search for “remote job” came up with a few great posts to help get your wheels turning about ways to potentially get your foot in the door with remote working opportunities.

3. contact a recruiter

Shameless plug here: I used to be a recruiter. And I love recruiters. I believe building a relationship with a recruiter is one of the best things you can do for your career. (But more on that another time.)

When kicking off your remote working career, it’s smart to reach out to a recruiter that specializes in helping place contingent workers. They can easily help guide you through the process of not only uncovering the right career path for you but also actually finding a viable opportunity that allows you the freedom and flexibility to break away from the corporate life.

Once you have an idea of what it is you want to do, the next step is to actually find the work. 

how to find your first side job (while still keeping your full-time gig)

Here’s the truth about contingent work: unless you partner with a recruiter and find an opportunity in a field you’re already working in, it’s not likely you’re going to transition overnight. It took me five months, and from what I can tell, that’s fairly fast to go from no experience to full-time self-employment. But there are a few reasons it didn’t take me as long as some to build my side business into a full-time gig.

First, I was organized. I spent a lot of time in the early stages researching the best channels for finding freelance copywriting work and then built an RSS feed through Feedly (for free) that updated me daily with the newest opportunities. Then, every night after my son went to bed, I spent time responding to 2 or 3 opportunities only. In retrospect, this part was critical. Plenty of people think playing the volume game makes the most sense and that you should just apply to as many jobs as possible. 

But I am a former recruiter and I am a big believer in quality over quantity. 

So instead of blasting out resumes and cover letters to 50+ opportunities, I found 2 or 3 where I really believed I could add value and spent 20-30 minutes crafting highly personalized emails to each. The result? With absolutely no writing experience other than blogging on LinkedIn, I received offers from 5 of the first 6 brands I contacted. It just goes to show that a personal touch makes a world of difference.

and that’s it…

The rest was just slowly taking on more work until I felt I had enough of a baseline to cover my family for a couple months while I transitioned into writing full-time.  And while I am only two months into doing this as my day job, I can tell you things are going great and I couldn’t be happier. I truly believe just about anyone can make the same transition I did. Hope this post helped you realize exactly how to make it happen.

want more career tips and resources like these? sign up for our newsletter.